benzyl (S)-(1-((4-methoxyphenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate | 24788-07-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (S)-(1-((4-methoxyphenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
• 英文别名: Cbz-Phe-4-methoxyanilide；benzyl N-[(2S)-1-(4-methoxyanilino)-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 24788-07-6
• 化学式: C₂₄H₂₄N₂O₄
• 分子量: 404.466
• InChiKey: LZUUHUCLSGYBFL-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (S)-(1-((4-methoxyphenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 在 氢溴酸 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (2S)-2-amino-N-(4-methoxyphenyl)-3-phenylpropanamide
  参考文献：
  名称：

  Enantioselective nickel-catalyzed conjugate addition of dialkylzinc to chalcones using chiral α-amino amides

  摘要：

  A series of alpha-amino amides derived from natural amino acids (alanine, valine, phenylalanine, isoleucine, and phenylglycine) have been synthesized and fully characterized. Their Ni(II) complexes prepared from Ni(acac)(2) catalyze the enantioselective conjugate addition of diethylzinc to chalcones in high yields and in good enantioselectivities (up to 84%). The side chain of the amino acid and the substituents in the amide nitrogen govern the enantioselectivity of the catalytic process. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.120
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 、 甲氧苯胺 在 Bacillus licheniformis serine protease Alcalase cross-linked enzyme aggregate 作用下， 以 甲基叔丁基醚 为溶剂， 反应 16.0h， 以88%的产率得到benzyl (S)-(1-((4-methoxyphenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
  参考文献：
  名称：

  Enzymatic Synthesis of C-Terminal Arylamides of Amino Acids and Peptides

  摘要：

  A mild and cost-efficient chemo-enzymatic method for the synthesis of C-terminal arylamides of amino acid and peptides is described. Using the industrial serine protease Alcalase under near-anhydrous conditions, C-terminal arylamides of N-Cbz-protected amino acids and peptides could be obtained from the corresponding C-terminal carboxylic acids, methyl (Me) or benzyl (Bn) esters, in hi-h chemical and enantio- and diastereomeric purities. Yields ranged between 50% and 95% depending on the size of the aryl substituents and the presence of electron-withdrawing substituents. Complete (alpha-C-terminal selectivity could be obtained even in the presence of various unprotected side-chain functionalities such as beta/gamma-carboxyl, hydroxyl, and guanidino groups. In addition, the use of the cysteine protease papain and the lipase Cal-B gave anilides in high yields. The chemo-enzymatic synthesis of arylamides proved to be completely free of racemization, in contrast to the state-of-the-art chemical methods.

  DOI：

  10.1021/jo900634g

文献信息

• An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry
  作者：Tarek S. Ibrahim、Israa A. Seliem、Siva S. Panda、Amany M. M. Al-Mahmoudy、Zakaria K. M. Abdel-Samii、Nabil A. Alhakamy、Hani Z. Asfour、Mohamed Elagawany

  DOI：10.3390/molecules25112501

  日期：——

  straightforward, mild and cost-efficient synthesis of various arylamides in water was accomplished using versatile benzotriazole chemistry. Acylation of various amines was achieved in water at room temperature as well as under microwave irradiation. The developed protocol unfolds the synthesis of amino acid aryl amides, drug conjugates and benzimidazoles. The environmentally friendly synthesis, short reaction

  使用通用的苯并三唑化学完成了在水中直接、温和且经济高效地合成各种芳基酰胺。在室温下以及在微波辐射下，在水中实现了各种胺的酰化。开发的协议展开了氨基酸芳基酰胺、药物偶联物和苯并咪唑的合成。环保合成、反应时间短、后处理简单、收率高、条件温和、无外消旋化是该协议的主要优点。
• [EN] CHEMO-ENZYMATIC SYNTHESIS OF A C-TERMINAL ARYL AMIDE OF AN AMINO ACID OR PEPTIDE<br/>[FR] SYNTHÈSE CHIMIO-ENZYMATIQUE D'UN ARYLAMIDE DE C-TERMINAL D'UN ACIDE AMINÉ OU PEPTIDE
  申请人：DSM IP ASSETS BV

  公开号：WO2009080631A2

  公开（公告）日：2009-07-02

  The present invention relates to a method for preparing an aryl amide, comprising reacting an aryl amine with a compound selected from N-protected amino acids and optionally N-protected peptides in the presence of a hydrolytic enzyme. The invention further relates to the use of a compound obtained in a method according to the invention in the manufacture of a diagnostic. In addition the invention relates to the use of a compound obtained in a method according to the invention as a substrate for a proteolytic enzyme.
• Enzymatic Synthesis of <i>C</i>-Terminal Arylamides of Amino Acids and Peptides
  作者：Timo Nuijens、Claudia Cusan、John A. W. Kruijtzer、Dirk T. S. Rijkers、Rob M. J. Liskamp、Peter J. L. M. Quaedflieg

  DOI：10.1021/jo900634g

  日期：2009.8.7

  A mild and cost-efficient chemo-enzymatic method for the synthesis of C-terminal arylamides of amino acid and peptides is described. Using the industrial serine protease Alcalase under near-anhydrous conditions, C-terminal arylamides of N-Cbz-protected amino acids and peptides could be obtained from the corresponding C-terminal carboxylic acids, methyl (Me) or benzyl (Bn) esters, in hi-h chemical and enantio- and diastereomeric purities. Yields ranged between 50% and 95% depending on the size of the aryl substituents and the presence of electron-withdrawing substituents. Complete (alpha-C-terminal selectivity could be obtained even in the presence of various unprotected side-chain functionalities such as beta/gamma-carboxyl, hydroxyl, and guanidino groups. In addition, the use of the cysteine protease papain and the lipase Cal-B gave anilides in high yields. The chemo-enzymatic synthesis of arylamides proved to be completely free of racemization, in contrast to the state-of-the-art chemical methods.
• Enantioselective nickel-catalyzed conjugate addition of dialkylzinc to chalcones using chiral α-amino amides
  作者：Jorge Escorihuela、M. Isabel Burguete、Santiago V. Luis

  DOI：10.1016/j.tetlet.2008.09.120

  日期：2008.11

  A series of alpha-amino amides derived from natural amino acids (alanine, valine, phenylalanine, isoleucine, and phenylglycine) have been synthesized and fully characterized. Their Ni(II) complexes prepared from Ni(acac)(2) catalyze the enantioselective conjugate addition of diethylzinc to chalcones in high yields and in good enantioselectivities (up to 84%). The side chain of the amino acid and the substituents in the amide nitrogen govern the enantioselectivity of the catalytic process. (c) 2008 Elsevier Ltd. All rights reserved.